


In Dean's Den

by Jamaican Princess (Rocquellan)



Category: Supernatural
Genre: Angst, First Time, M/M, OMC - Freeform, Possessive Behavior, Possessive Dean Winchester, Prelude to Sam/Dean, Protective Dean Winchester, Some Humor
Language: English
Status: Completed
Published: 2015-05-25
Updated: 2015-05-25
Packaged: 2018-04-01 03:35:35
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,788
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4004338
Author URL: https://archiveofourown.org/users/Rocquellan/pseuds/Jamaican%20Princess
Summary: <blockquote class="userstuff">
              <p>Sam wants to sleep with some guy that he likes from school and Dean's all for it, except he has to be there to make sure things go smoothly, no matter what Sammy wants to say about it.</p>
            </blockquote>





	In Dean's Den

**Author's Note:**

> I'm still on that possessive Dean streak! :D
> 
> I don't have a beta so concrit would be appreciated. Tnx!

It wasn’t fair. Dean could be such an _asshole_ sometimes. Sam stormed into the kitchen of their current motel and threw his bag on the table harshly, wanting to get away from and punch his big brother in the face at the same time.

“Sam!” Dean bellowed, slamming the door shut behind him with a kick of his booted foot. This argument has been going on since Dean picked Sam up from school, having to look for him since he wasn’t at the front gate like usual. Finding Sammy under the bleachers with a senior jock’s - _a jock!_ \- tongue down his throat and his hands in places Dean doesn’t even want to name almost caused him to explode with rage. He was about to punch the guy’s face in until he saw that look on Sammy’s face. That barely subtle bitchface that meant Dean would be the one getting his ass kicked if he continued his train of thought. “I’m talking to you, Sammy!”

“Fuck off, Dean,” Sam growled while he filled a glass with water from the tap. The water here tasted like shit but he didn’t care at the moment. Getting angry always left him thirsty. He was thirsty a lot.

“Watch your damn mouth,” Dean warned as he walked around the kitchen table. “What the hell was that guy doing to you, anyways?”

Sam turned around to face Dean, a snare on his face. “It’s called first base, Dean. You know, the kissing and touching? Unlike you I can’t jump to sex in any corner when the mood strikes.”

“So you plan to sleep with him then.” Dean leaned against the kitchen counter, his stance stiff.

Sam flung the glass into the the sink before glaring at his brother. “What the hell did it look like?”

Dean deflated, suddenly resigned. “You’re a virgin, Sammy…”

Sam scowled. “‘Am not!”

Dean rolled his eyes and his look said it all. “Yes you are. I’d know if you’re bumping uglies with some dude, trust me.”

“I had sex with a girl before, Dean,” Sam pouted.

Dean snickered. “No, Sammy. Serena Jones slept with me, not you, remember?”

Sam deflated at that. “Look, I like Brendan, ok?”

“A jock, Sammy? Really?” Dean just had to know. He always had this mindless caveman vibe he got from jocks and he honestly couldn’t see his virgin Sammy hooking up with a jock for his first time. He’d had guessed the president for the mathletes or something...except Sammy was the president for the mathletes. Fuck!

Sam sat around the kitchen table and sighed irritably before looking up at Dean across the table. “He doesn’t fit whatever stereotype you’re putting him in, Dean. He’s smart and funny. We met in the library and I was kinda surprised too that this muscle bound guy in a jersey shirt sitting beside me was reading up on biophysics and chemistry. We got to talking and it was obvious he liked me. We met sometimes and did stuff together, then you happened.”

Dean sat across from his little brother, who was angling his head down so his hair hid his face. “Look, I’m not against you having a boyfriend, Sammy. What I want to know is if you plan to sleep with him.”

Sam looked up at Dean. “Yes.”

Dean nodded. “Fine, tell me when.”

Sam looked at Dean wide eyed. “W-what?”

“Tell me when, Sammy. I’m all for you bumping uglies with some dude if you want but not by yourself.”

“Dean…” Sam laughed incredulous. “Do you hear what you’re saying?”

Dean sighed, put upon, then he explained clearly and warningly, “I’m there to supervise your first time with this guy Sammy or there’ll be no first time. I’m not asking you, I’m telling you. Now take it or leave it, it’s not up for negotiation. This guy probably has way more experience than you, there’s lots of way you could get taken advantage of or hurt and that’s not happening on my watch.”

Dean sat back with his arms crossed and a look that said he’s not above punching Sam’s lights out if he doesn’t listen and Sam knows he’s good for it. When Dean’s angry at him he likes to throw hits. Dean doesn’t do well with anger. “I hear you, ok? But tell me why you’re so adamant about this. You were fifteen your first time and I’m seventeen. I can take care of myself, Dean.”

“Anything can happen when your partner’s twice your muscle mass, Sammy. I’m not taking the risk.”

Sam gave his brother an exasperated look. Learning some obscure language was sometimes easier than Dean-logic. “He’s not gonna force me or anything. Brendan’s actually a pretty nice guy.”

Dean growled low in his throat and Sam was taken aback by it.

“He fucks you -or whatever- _here_ where I can supervise or he can’t touch you. I’ll break every bone in his body if he does it without my permission.”

Sam nodded just to get Dean to shut up. This was so fucked up it wasn’t even funny.

……….

So, the day almost came. Sam really likes Brendan, like a lot. It’s been two weeks since that crazy talk with Dean, who allowed him to go on sorta-dates with Brendan and would know any lines they would cross. As long as they stayed behind _that_ one there wasn’t a problem.

But Brendan was really sweet and cool and Sam was getting more sexually frustrated by the day. He was so irritated he was tempted to go through with Dean’s crazy idea, just to not have his brother breathing down his neck and hitting him for not following his one rule.

And to prevent blue balls.

One rule, negotiable rules unlike the ultimatums dad gave, which was why Dean was the way lesser of two evils. And he did not mean that literally. Sam could see that Brendan wanted badly to get in his pants too, which made it a little easier when he told Dean a simple OK over dinner one night. Dean didn’t ask what he was talking about, just nodded and went to the bedroom. When Sam went to bed he could see the detritus of an impending roll in the hay. The lube and condoms sat innocently on the dresser, staring at him the entire night. Sam closed his eyes with a sigh and went to bed.

……….

Sam stood outside the door while Brendan knocked, both of them holding hands and giving each other nervous glances. Dean answered and gave Brendan an obvious once over. Sam squeezed his hands and he could tell it calmed his sorta-boyfriend somewhat. 

He and Dean will be gone in a few weeks anyway when dad was through hunting, no need to get too attached about it no matter how much he wanted to. It was his first time, it should have been more special than Dean standing over them like an avenging angel. 

“H-hi. I’m Brendan, Sir.”

Brendan stretched his hand for a shake and Dean looked at it before pulling the guy’s hand in a too firm grip. “Dean Winchester.”

Brendan nodded and Dean stepped aside so they could file inside. Sam was glad Dean wasn’t being a bigger dick than usual about it.

“Want anything to drink before you kids start?” Dean asked, the look on his face clearly saying it was his way or the highway and he wasn’t too happy about it either.

Brendan shook his head no and Sam smiled. “No we don’t. Can we go now?”

Dean pointed towards the bedroom. “Lead the way.”

Jesus fuck but Dean was really gonna stand there and watch Sam take a dick up the ass for the first time.

Brendan followed Sam’s lead and they sat on his bed for a few awkward moments, trying to ignore the elephant in the room that was staring at them from beside the bedroom door.

“Well?” Dean asked and both head snapped to look at him.

“Um...” Brendan started and Sam kissed him, throwing both hands around those firm shoulders and leaning into Brendan so Dean was out of their line of sight. Sam had always liked how Brendan kiss, it was really nice. Brendan’s hand came up around him a moment later and Sam relished the feel of those strong arms holding on to him. The kiss continued for a while and Sam was hard in his jeans. He could tell Brendan was too. He leaned into Brendan and Brendan drag-lifted him until he was in his lap, straddling him. Sam could almost forget Dean was in the room. Almost...

Dean cleared his throat and Sam sighed after breaking the kiss.

“No excessive use of strength.”

“You fuck like you fight Dean, I’ve seen you,” Sam growled, glaring at his brother.

“Not to virgins, Sammy.” Dean had a saccharine smile on his face and Sam just wanted to punch him. He shouldn’t even _be_ here.

“Um, fine. Ok,” Brendan muttered and Sam turned back to him, a smile on his face.

They started kissing again and after a while Sam found himself grinding against Brendan, both their clothed hard ons getting some sweet friction. It wasn’t enough but it felt so damn good. Sam grabbed the headboard and started grinding in earnest, chasing his building orgasm.

“Oh fuck...” Sam moaned with his head buried in Brendan’s neck. Brendan’s hands were on his waist, holding tight and his breath puffed into Sam’s own neck in stuttered gasps. 

“Language, Sammy.”

“ _Jesus Christ._ ” Sam was exasperated. Dean could be such a buzzkill it wasn’t even funny. But he wanted to come, felt it and he didn’t stop, wouldn’t allow Dean to make him stop with his unsubtle bullshit.

“I want you to fuck me, Brendan,” Sam whispered harshly into Brendan’s ear while he rode him, his technique having less finesse and a lot more rut as they progressed. The pheromones were fucking up his headspace and he turned to look at Dean, his impassively cool brother standing there like he had any damn right to be there. His brain to mouth filter was shot to shit and his eyes didn’t leave Dean as he grunted. “Want you to open me up and put your big fucking dick inside and make me feel it...” And something in Sam’s messed up head wasn’t sure who he was really talking to.

“Yeah, Sam...” Brendan moaned and Sam turned his full attention back to the guy under him. His hands tightened on Brendan’s shoulder and the headboard. He was so damn close he could feel it tingling up his spine.

“I’m gonna...” Sam moaned, his hips stuttering and his head dropped, it was almost too much. Brendan grabbed his crotch and squeezed and Sam turned to look at Dean as his world explode in shards of whites behind his eyelids and a scream that had him arching his back and coming in his pants. His muscles tensed and his hair flew every which way as he rode out his orgasm, dimly realizing that Brendan was coming too. He rolled over until he was on his back on the bed, breathing harshly and boneless. Brendan shifted like he wanted to move with Sam but Dean had to interrupt.

“Hey, clean up before you go any further.”

“What?” Sam asked mystified as Dean passed him a box of Kleenex via Brendan. “Why should I...?”

“Hey, it’s my turn to do laundry. Humor me, ok Sammy?”

Sam sighed explosively. He did clean up though, bashful when Brendan took his pants and underwear off and wiped the come off his pants as much as possible.

“I’m sorry,” Sam mouthed silently and Brendan smiled, not the grimace or weirdness Sam expected he would be sporting. But soon Sam was fully naked on the bed, getting rid of his shirt too and he smiled when Brendan gave him a very appreciative look, like he was definitely liking what he saw.

“Um...” Brendan cleared his throat. “Can I blow you, Sam?”

Brendan talked loud enough that Sam knew he wanted Dean to hear and Sam realized Brendan didn’t want to do anything suddenly that might cause Dean to smite him. Dean was such a pest, but he smiled up at Brendan. “Sure, I’d like that.”

Sam settled himself comfortably, widening his legs so Brendan could get between after leaving himself in only his briefs. His cock hardened instantly as soon as that mouth got him in a good suction, working up and down. Sam threw his head back and gripped the sheets with both fists, breathing harshly through his nose. Sam bit his bottom lip, whimpering as he looked down to see his length buried so far down Brendan’s throat the guy’s nose was rubbing in his pubes.

“God...” Sam moaned. He had his eyes closed, until he opened them and was staring cross eyed at Dean. When his vision came into focus he realized Dean was frowning with his hands crossed against his chest, watching them intently. It pinged something down his spine to know his brother had his eyes on him, that Dean was watching him get blown, watching his dick disappear into a very willing mouth.

And Dean was obviously hard, unless he had his flashlight in the front of his pants, which Sam doubted was the case.

“Oh fuck...” Sam groaned when Brendan threw a leg over his shoulder and sucked harder, deeper. He was just trying to keep his head above the sea of feelings and emotions coursing through his system. The rushing in his ears clashed with the sounds of his own come hither voice and the sucking sounds Brendan happily made in his ministrations.

“I’m...” Sam managed as he closed his eyes and squeezed Brendan’s shoulders. God, but it was too much too soon.

Brendan pulled off with an audible pop and shoved up to kiss Sam, hard. Sam returned the kiss with fervor, some part of him bemoaning the loss of sweet mouth friction. He could tell from his movements Brendan was freeing his own self, settling between his legs and rubbing against him. Sam could feel the blunt head rubbing all over him and he sort of liked the feel.

Brendan stopped to grab the lube and Sam looked over at Dean, biting his lower lip in minor indecision. Sam wasn’t afraid of the idea of sex, but sex for the first time was a reality that was settling in and he wasn’t too sure suddenly. Maybe all he wanted was to get off? The blowjob? 

Maybe...

Brendan rolled on the condom and was fingering at his entrance. Sam looked at him and looked at Dean. He wasn’t sure what Dean saw but his big brother suddenly stalked over to them, shoving Brendan off him and throwing him his clothes.

“What-?!” Brendan squeaked when he fell to the ground.

“Hey! He doesn’t want to. Get dressed and go home.”

“Wait, Sam...?” Brendan asked expectantly and Sam looked at him. He wasn’t sure what Brendan saw either but he deflated, shoulders slumping in resignation. 

“Was I hurting you or something?” Brendan asked as he pulled his shirt over his head.

“No, no.” Sam sniffled. “Nothing like that.”

“First time jitters?” Brendan asked softly.

Sam looked at Dean, who was staring down at him in concern. He’s suddenly so grateful for his brother’s presence his heart swells with it. Then he looked at Brendan, “Yeah, I’m so sorry...”

Brendan nodded. “It’s fine, I would have stopped if you said so, Sam.” He zipped up his pants. “But I’m sorry too,” he looked at Dean then. “This isn’t gonna work out.”

Sam nodded, looking down at the sheets and clenching his hands. “I know, I’m sorry...”

“It’s ok, Sam. Maybe someday you’ll find the right person for you...both,” Brendan finished as he put himself together.

Sam didn’t know if that was possible. “Yeah, sure.”

Sam burrowed under the covers as Dean saw Brendan out. He felt too tight in his own skin, even as Dean came back with orange juice that he left on the dresser for him. His brother sat on the bed and ruffled his hair under the covers.

“Hey, you ok under there, kiddo?” Dean asked.

Sam brought the covers down to under his chin and looked up at Dean. “Yeah, I think so.”

“Wanna go get some ice cream?”

Sam smiled, sitting up now. There was another, newer elephant in the room that needed addressing, but for now it would be glossed over and ignored in true Winchester fashion. “Yeah, that sounds great.”

“Not until you shower first though, you reek!”

Sam laughed as Dean pulled the sheets from off him. “Jerk.”

“Bitch.”


End file.
